Octreotide

Octreotide
	3D structure of octreotide. PDB: 6VC1
Clinical data
Trade names	Sandostatin, Bynfezia Pen, Mycapssa, others
AHFS/Drugs.com	Monograph
MedlinePlus	a693049
License data	US DailyMed: Octreotide;
Pregnancy; category	AU: C; ;
Routes of; administration	Subcutaneous, intramuscular, intravenous, by mouth
ATC code	H01CB02 (WHO) ;
Legal status
Legal status	AU: S4 (Prescription only); CA: ℞-only; UK: POM (Prescription only); US: ℞-only; EU: Rx-only;
Pharmacokinetic data
Bioavailability	60% (IM), 100% (SC)
Protein binding	40–65%
Metabolism	Liver
Elimination half-life	1.7–1.9 hours
Excretion	Urine (32%)
Identifiers
	IUPAC name (4R,7S,10S,13R,16S,19R)-10-(4-aminobutyl)-19-; [[(2R)-2-amino-3-phenyl-propanoyl]amino]-16-; benzyl-N-[(2R,3R)-1,3-dihydroxybutan-2-yl]-7-; (1-hydroxyethyl)-13-(1H-indol-3-ylmethyl)-6,9,12,; 15,18-pentaoxo-1,2-dithia-5,8,11,14,17-; pentazacycloicosane-4-carboxamide;
CAS Number	83150-76-9 ; 135467-16-2 (pamoate); as acetate: 79517-01-4;
PubChem CID	Octreotide; as acetate: 448601;
IUPHAR/BPS	2055;
DrugBank	DB00104 ; as acetate: DBSALT000130;
ChemSpider	395352 ; as acetate: 5293182;
UNII	RWM8CCW8GP; as acetate: 75R0U2568I;
KEGG	D00442 ; as acetate: D06495;
ChEBI	CHEBI:7726;
ChEMBL	ChEMBL1680 ; as acetate: ChEMBL1200480;
CompTox Dashboard (EPA)	DTXSID0048682 ;
Chemical and physical data
Formula	C49H66N10O10S2
Molar mass	1019.25 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES C[C@H]([C@H]1C(=O)N[C@@H](CSSC[C@@H](C(=O)N[C@H](C(=O)N[C@@H](C(=O)N[C@H](C(=O)N1)CCCCN)Cc2c[nH]c3c2cccc3)Cc4ccccc4)NC(=O)[C@@H](Cc5ccccc5)N)C(=O)N[C@H](CO)[C@@H](C)O)O;
	InChI InChI=1S/C49H66N10O10S2/c1-28(61)39(25-60)56-48(68)41-27-71-70-26-40(57-43(63)34(51)21-30-13-5-3-6-14-30)47(67)54-37(22-31-15-7-4-8-16-31)45(65)55-38(23-32-24-52-35-18-10-9-17-33(32)35)46(66)53-36(19-11-12-20-50)44(64)59-42(29(2)62)49(69)58-41/h3-10,13-18,24,28-29,34,36-42,52,60-62H,11-12,19-23,25-27,50-51H2,1-2H3,(H,53,66)(H,54,67)(H,55,65)(H,56,68)(H,57,63)(H,58,69)(H,59,64)/t28-,29-,34-,36+,37+,38-,39-,40+,41+,42+/m1/s1 ; Key:DEQANNDTNATYII-OULOTJBUSA-N ;
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Octreotide, sold under the brand name Sandostatin among others, is an octapeptide that mimics natural somatostatin pharmacologically, though it is a more potent inhibitor of growth hormone, glucagon, and insulin than the natural hormone. It was first synthesized in 1979 by the chemist Wilfried Bauer, and binds predominantly to the somatostatin receptors SSTR2 and SSTR5.^[4]

It was approved for use in the United States in 1988.^[2]^[1] Octreotide (Mycapssa) was approved for medical use in the European Union in 2022.^[3] As of June 2020^[update], octreotide (Mycapssa) is the first and only oral somatostatin analog (SSA) approved by the FDA.^[5] It is on the World Health Organization's List of Essential Medicines.^[6]

^ ^a ^b Cite error: The named reference Sandostatin label was invoked but never defined (see the help page).
^ ^a ^b Cite error: The named reference Bynfezia Pen label was invoked but never defined (see the help page).
^ ^a ^b "Mycapssa EPAR". European Medicines Agency. 14 September 2022. Retrieved 24 December 2022. Text was copied from this source which is copyright European Medicines Agency. Reproduction is authorized provided the source is acknowledged.
^ Hofland LJ, Lamberts SW (January 1996). "Somatostatin receptors and disease: role of receptor subtypes". Baillière's Clinical Endocrinology and Metabolism. 10 (1): 163–176. doi:10.1016/s0950-351x(96)80362-4. hdl:1765/60433. PMID 8734455.
^ Cite error: The named reference Chiasma Mycapssa PR was invoked but never defined (see the help page).
^ World Health Organization (2023). The selection and use of essential medicines 2023: web annex A: World Health Organization model list of essential medicines: 23rd list (2023). Geneva: World Health Organization. hdl:10665/371090. WHO/MHP/HPS/EML/2023.02.

[Sandostatin_label-1] Cite error: The named reference Sandostatin label was invoked but never defined (see the help page).

[Bynfezia_Pen_label-2] Cite error: The named reference Bynfezia Pen label was invoked but never defined (see the help page).

[Mycapssa_EPAR-3] "Mycapssa EPAR". European Medicines Agency. 14 September 2022. Retrieved 24 December 2022. Text was copied from this source which is copyright European Medicines Agency. Reproduction is authorized provided the source is acknowledged.

[4] Hofland LJ, Lamberts SW (January 1996). "Somatostatin receptors and disease: role of receptor subtypes". Baillière's Clinical Endocrinology and Metabolism. 10 (1): 163–176. doi:10.1016/s0950-351x(96)80362-4. hdl:1765/60433. PMID 8734455.

[Chiasma_Mycapssa_PR-5] Cite error: The named reference Chiasma Mycapssa PR was invoked but never defined (see the help page).

[WHO23rd-6] World Health Organization (2023). The selection and use of essential medicines 2023: web annex A: World Health Organization model list of essential medicines: 23rd list (2023). Geneva: World Health Organization. hdl:10665/371090. WHO/MHP/HPS/EML/2023.02.

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